The case examines the liquidity issues that J. C. Penney (JCP) experienced in 2012 and 2013 following a decline in sales and profits over several years. Despite once being a highly profitable and growing company, the increasing pressures of competition led to changes in strategy and in management that were insufficient to return the company to the consistent financial results it had previously enjoyed. While sales and profits waned, the cash balance also suffered, and Wall Street analysts began expressing liquidity concerns as the company wrestled with having enough cash on hand to cover daily operating needs. Students are asked to calculate a time series of quarterly liquidity and leverage ratios to illustrate the declining financial condition of the company. They are further challenged to weigh the benefits and drawbacks of raising equity versus debt as a solution for the company’s lack of liquidity. To assess the amount of external capital required, students are asked to use a sources and uses analysis that provides intuition for the cash flow challenges facing the company. Set against the background of an iconic retailer, the case provides an engaging context in which to discuss the need for a major capital structure decision due to operational challenges.